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Oxidative Coupling of Aryl Boron Reagents with sp 3 ‐Carbon Nucleophiles: The Enolate Chan–Evans–Lam Reaction
Author(s) -
Moon Patrick J.,
Halperin Heather M.,
Lundgren Rylan J.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201510558
Subject(s) - nucleophile , electrophile , aryl , chemistry , amide , halogen , boron , medicinal chemistry , methylene , coupling reaction , reagent , combinatorial chemistry , organic chemistry , catalysis , alkyl
Reported is a versatile new oxidative method for the arylation of activated methylene species. Under mild reaction conditions (RT to 40 °C), Cu(OTf) 2 mediates the selective coupling of functionalized aryl boron species with a variety of stabilized sp 3 ‐nucleophiles. Tertiary malonates and amido esters can be employed as substrates to generate quaternary centers. Complementing either traditional cross‐coupling or S N Ar protocols, the transformation is chemoselective in the presence of halogen electrophiles, including aryl bromides and iodides. Substrates bearing amide, sulfonyl, and phosphonyl groups, which are not amenable to coupling under mild Hurtley‐type conditions, are suitable reaction partners.